3-(Trifluoromethyl)benzaldehyde → 3,3-bis(4-fluorophenyl)-1-(2-oxo-2-{(4aS,7aS)-1-[3-(trifluoromethyl)benzyl]octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl}ethyl)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of product from Example 210A (0.2 g, 0.455 mmol) in dichloroethane (10 mL) was added 3-(trifluoromethyl)benzaldehyde (0.135 g, 0.774 mmol), sodium triacetoxyborohydride (0.145 g, 0.683 mmol), and a few drops of acetic acid. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and washed with saturated aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, concentrated and purified by silica gel chromatography eluting with 2-5% methanol/dichloromethane. 1H NMR (400 MHz, pyridine-d5, temperature 90° C.) δ ppm 7.63-7.72 (m, 1H), 7.55-7.63 (m, 4H), 7.47-7.58 (m, 2H), 7.33-7.45 (m, 1H), 7.00-7.08 (m, 4H), 4.13-4.33 (m, 2H), 3.66-3.77 (m, 1H), 3.51-3.65 (m, 3H), 3.27-3.65 (m, 4H), 2.87-3.15 (m, 1H), 2.73-2.80 (m, 2H), 2.45-2.57 (m, 1H), 2.06-2.26 (m, 2H), 1.23-1.56 (m, 4H); MS (ESI+) m/z 599 (M+H)+.

Provenance & Evidence